The study deals with the question of the relationships among the conception of human nature, its cognition and education in Michel de Montaigne’s Essays. In the series of essays, Montaigne repeatedly rejects attempts to base his conception of human nature on antic- scholastic traditions operating with the general concepts of man. Montaigne’s specific Christian scepticism (“new pyrrhonism”) is the starting point and the argumentative method for rejecting the reliability of general concepts and definitions. Whereas scholastic (as well as predominantly entire ancient) philosophy assumed the existence of an ideal species to be the essence that determines each individual’s essential characteristics, Montaigne sees, on the contrary, man in the state of constant transformation, transition as crucial to understanding the human situation. This fundamentally transforms the traditional understanding of the relationship between a pattern and its imitation, into a relationship that has not only epistemological but also pedagogical and moral implications. Montaigne argues that subjectivity cannot be understood against the background of a general pattern, but only from itself, from ambiguities and paradoxes that, on the contrary, exclude, elude any generalization. Human nature cannot be captured in a general concept, it can only be exemplified from a specific experience. Thus, man is much more a transition (from one form to another) than a substance. The aim of this study is to show Michel de Montaigne as a modern and up-to-date thinker who, through his rhetoric and his way of grasping pedagogical issues, has opened up a number of educational questions that are relevant today: for example, how to understand the educational goal in a practical and informal way, how to work in education with the unique and the non-generalizable, and how to consider the relationship between knowledge and action.